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Pleasure was born in Hartford, Connecticut. His parents Robert and Evelyn Pleasure were originally from Louisiana, but moved to Hartford so Robert could attend Yale Divinity School from which he graduated in 1961. The family then moved to Guilford, Connecticut when young Pleasure was 7 years old. Pleasure began playing piano at age four and studied piano under Carol Wright from age seven to 17.

Frequent trips to Louisiana to visit family gave Pleasure a deep exposure to and appreciation for Gospel music as many of his relatives were active in church, and gospel music was the soundtrack of their lives. And it was on these trips that he also experienced first hand the inequalities of a still segregated south. A black family traveling through the south in those times could not stop at a hotel for the night, so the family would make these trips nonstop.

By the time Pleasure was a teenager, he had become proficient in trumpet, guitar, drums and violin as well. He composed his first song at age 12. He accompanied his father (an accomplished tenor) at all the Guilford high school's graduations from 1975–80 and was active in his high school's music programs. Pleasure holds a Bachelor of Arts degree in music from the University of Connecticut (1986)